Preheat oven to 350°F. Mix together goat cheese and pesto on a small bowl; set aside. Cut about 1/4 inch off top of tomato and discard "cap." Drizzle olive oil on tomato. Season with salt and pepper.

Bake tomatoes on baking sheet for about 45 minutes, or until tender. (They should not cook so long that they begin to fall apart.) Remove from oven and top with goat cheese mixture. Sprinkle with basil and broil for about 2 minutes, or until cheese begins to turn golden and bubble. Serve immediately.